2-O-octanoylsucrose

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 2-O-octanoylsucrose
• 英文别名: octanoyl(-2)Glc(a1-2b)Fruf；[(2R,3R,4S,5S,6R)-2-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] octanoate
• 化学式: C₂₀H₃₆O₁₂
• 分子量: 468.499
• InChiKey: YOBVDYPPNNHXEG-OASARBKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  196
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  辛酸乙烯酯 、 蔗糖 在 disodium hydrogenphosphate 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以59.8%的产率得到2-O-octanoylsucrose
  参考文献：
  名称：

  改善蔗糖脂肪酸单酯的合成

  摘要：

  AbstractThe base‐catalyzed synthesis of four sucrose fatty acid esters (caprylate, laurate, myristate, and palmitate) was performed in dimethylsulfoxide by transesterification of sucrose with the corresponding vinyl esters using disodium hydrogen phosphate as catalyst. In using a molar ratio sucrose/vinyl ester 4∶1 and mild reaction conditions (40°C and atmospheric pressure), yields were higher than 85%. The isolated sucroesters had a higher percentage of monoesters (≥90%) and a lower content of diesters in comparison with commercial derivatives. In all cases, 2‐O‐acylsucrose was the major product (≥60%) in the monoester fraction.

  DOI：

  10.1007/s11746-001-0300-5

文献信息

• Transesterification of Sucrose in Organic Medium: Study of Acyl Group Migrations
  作者：Valérie Molinier、Krzysztof Wisniewski、Alain Bouchu、Juliette Fitremann、Yves Queneau

  DOI：10.1081/car-120026466

  日期：2003.12.31

  of sucrose fatty acid esters to undergo intramolecular migrations in organic medium and the regioselectivity of some transesterifications of sucrose were investigated by HPLC, in situ NMR spectroscopy and preparative methods. Extensive acylation on secondary positions of the glucose moiety followed by migrations is general for base catalysed transesterification. The stability of 3‐ and 6‐O‐acyl derivatives

  通过HPLC，原位NMR光谱和制备方法研究了蔗糖脂肪酸酯的葡萄糖部分上的酰基在有机介质中发生分子内迁移的趋势以及一些蔗糖的酯交换反应的区域选择性。对于碱基催化的酯交换反应，通常在葡萄糖部分的次要位置上进行广泛的酰化，然后进行迁移。在一系列条件下研究了3-和6- O-酰基衍生物的稳定性，这两个异构体在热力学上比其他异构体更受青睐。结果表明，在有机碱性介质中，水的存在会催化OH-3处的酯向OH-6的迁移，而OH-6处的酯在酸性或碱性条件下显得更稳定。
• Esterification of unprotected sucrose with acid chlorides in aqueous medium: kinetic reactivity versus acyl- or alkyloxycarbonyl-group migrations
  作者：Sophie Thévenet、Angelika Wernicke、Stanislaw Belniak、Gérard Descotes、Alain Bouchu、Yves Queneau

  DOI：10.1016/s0008-6215(99)00079-8

  日期：1999.5

  between formation, migration and hydrolysis of sucrose mono-esters and -carbonates confirmed that the pre-eminent reactivity of some secondary positions persists in aqueous medium, and in particular, OH-2, even though fast subsequent migrations finally enrich the mixture in compounds substituted at the primary positions. The reaction was also shown to depend strongly on the starting sucrose concentration

  摘要对蔗糖单酯和碳酸酯的形成，迁移和水解之间竞争的研究证实，即使在随后的快速迁移中，某些次要位置的反应仍在水性介质（尤其是OH-2）中持续存在。使混合物中的主要位置取代的化合物富集。与较小的链相比，在疏水性酰化剂的情况下，该反应还显示出强烈依赖于起始蔗糖的浓度，从而提供了更高的取代衍生物。
• Hydrophobic Effect Driven Esterification of Sucrose in Aqueous Medium¹
  作者：Sophie Thévenet、Gérard Descotes、Alain Bouchu、Yves Queneau

  DOI：10.1080/07328309708007347

  日期：1997.5

  derivatives, surfactants, or non-caloric fat substitutes.2 But although such potential commercially attractive sucrose derived molecules can be targeted, methods consistent with low-cost sucrouse diversification have still to be found. The issue of the solvent being critical, we have been interested in evaluating water as a possible solvent for some transformations of sucrose, and we report herein some

  蔗糖是化学上有吸引力的分子，因为它是纯净，丰富，廉价且由可再生资源生产。在其衍生物中，蔗糖酯是糖化学增值的重要靶标，无论是可聚合衍生物，表面活性剂还是非热量脂肪替代品。2尽管可以靶向这种潜在的商业上有吸引力的蔗糖衍生分子，但方法与低成本一致子公司多元化仍然有待发现。溶剂的问题是至关重要的，我们一直有兴趣评估水作为蔗糖某些转化的可能溶剂，并且我们在此报告了在碱性水介质中该糖酯化的一些初步结果。1.于1996年7月21日至26日在意大利米兰举行的第十八届国际碳水化合物研讨会上发表。
• EP1550667
  申请人：——

  公开号：——

  公开（公告）日：——
• Improved synthesis of sucrose fatty acid monoesters
  作者：M. Angeles Cruces、Francisco J. Plou、Manuel Ferrer、Manuel Bernabé、Antonio Ballesteros

  DOI：10.1007/s11746-001-0300-5

  日期：2001.5

  AbstractThe base‐catalyzed synthesis of four sucrose fatty acid esters (caprylate, laurate, myristate, and palmitate) was performed in dimethylsulfoxide by transesterification of sucrose with the corresponding vinyl esters using disodium hydrogen phosphate as catalyst. In using a molar ratio sucrose/vinyl ester 4∶1 and mild reaction conditions (40°C and atmospheric pressure), yields were higher than 85%. The isolated sucroesters had a higher percentage of monoesters (≥90%) and a lower content of diesters in comparison with commercial derivatives. In all cases, 2‐O‐acylsucrose was the major product (≥60%) in the monoester fraction.